Hydrochloric Acid → (13E)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiran-2-yl)ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

Participants

Reaction Steps

To a solution of Cryptophycin 1 (500 mg) in 3 mL of 1,2-dimethoxyethane was added 60 μL of concentrated HCl. The mixture was stirred at room temperature for 18 h, potassium carbonate (50 mg) was added, and the mixture was stirred for an additional 2 h, then filtered and evaporated. The residue was subjected to reversed-phase HPLC (Alltech Econosil C18, 250 mm×22 mm column, flow rate 5 mL/min, 20 mg/injection, UV detection at 254 nm) using 3:1 MeCN/H2O to give 433 mg of Cryptophycin 8 (tR 25 min) and 16 mg of Cryptophycin 27 (tR 21 min)).

Provenance & Evidence